6alpha-acetoxy-1beta-hydroxyguaia-4(15),10(14),11(13)-trien-8alpha,12-olide - Compound Card

6alpha-acetoxy-1beta-hydroxyguaia-4(15),10(14),11(13)-trien-8alpha,12-olide

Select a section from the left sidebar

6alpha-acetoxy-1beta-hydroxyguaia-4(15),10(14),11(13)-trien-8alpha,12-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CC(=O)O[C@H]1[C@H]2[C@@H](OC(=O)C2=C)CC(=C)[C@@]2([C@H]1C(=C)CC2)O
InChI InChI=1S/C17H20O5/c1-8-5-6-17(20)9(2)7-12-13(10(3)16(19)22-12)15(14(8)17)21-11(4)18/h12-15,20H,1-3,5-7H2,4H3/t12-,13+,14-,15-,17-/m0/s1
InChIKey GYRJPATVNGOBRW-PFFSRIRZSA-N
Formula C17H20O5
HBA 5
HBD 1
MW 304.34
Rotatable Bonds 1
TPSA 72.83
LogP 1.67
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.53
Exact Mass 304.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Brocchia cinerea Asteraceae Plantae 282208

Showing of synonyms

  • Jakupovic J, Aal MA, et al. (1988). Further glaucolides and other sesquiterpene lactones from Brocchia cinerea.. Phytochemistry,1988,27(7),2219-2224. [View]
Pubchem: 14137541
Nmrshiftdb2: 70018567

No compound-protein relationship available.

Structure

SMILES: C=C1C(=O)OC(C12)CC(=C)C3C(C2)C(=C)CC3

Level: 0

Mol. Weight: 304.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.6
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.65
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.52

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.45
Plasma Protein Binding
46.02
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
9.82
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.01
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.12
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.74
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-0.45
Rat (Acute)
3.41
Rat (Chronic Oral)
1.83
Fathead Minnow
3.92
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
337.01
Hydration Free Energy
-6.87
Log(D) at pH=7.4
0.89
Log(P)
1.08
Log S
-2.88
Log(Vapor Pressure)
-6.72
Melting Point
147.94
pKa Acid
6.85
pKa Basic
4.74
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8311
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8311
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8077
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8077
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8067
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8067
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7903
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7903
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7854
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7854
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7709
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7709
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7564
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7564
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7561
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7561
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7489
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7489
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7482
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7482
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7401
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7401
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 2 0.7369
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 2 0.7369
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7363
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7363
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7358
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7358
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7347
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7347
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7322
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7322
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7295
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7295
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7275
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7275
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7272
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7272
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7176
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7176
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7148
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7148
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7141
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7141
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7114
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7114
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7099
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7099
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7073
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7073
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 2 0.7068
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 2 0.7068
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7068
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7068

Download SDF